


leaders with benefits

by mocha (kokomocha)



Category: Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters: Sword & Shield | Pokemon Sword & Shield Versions
Genre: Anal Fingering, Anal Sex, Awkward Boners, Bad Puns, Battle, Bed Sex, Bedroom Sex, Bisexual Male Character, Blow Jobs, Blue Balls, Blushing, Cock Tease, Come Shot, Come Swallowing, Competition, Desperation, Desperation Play, Dominatrix, Drunken Flirting, Dubiously Consensual Blow Jobs, Embarrassment, Erections, F/M, Femdom, Flirting, Hickeys, Hormones, Horniness, Light BDSM, Light Bondage, Lube, M/M, Making Out, Masturbation, Moaning, Mutual Masturbation, Mutual Pining, My First Work in This Fandom, Neck Kissing, Older Man/Younger Man, One Shot, Oral Sex, Orgasm, Orgasm Control, Orgasm Delay/Denial, POV Second Person, PWP, Pain, Painful Sex, Penis In Vagina Sex, Plot What Plot/Porn Without Plot, Pokemon Battle, Pokemon References, Power Play, Prostate Massage, Restraints, Rope Bondage, Rough Sex, Simultaneous Orgasm, Sloppy Makeouts, Smut, Spit As Lube, Strip Tease, Teasing, Touching, Uncircumcised Penis, Underage Drinking, Underage Masturbation, Underwear, Wine, tipsy
Language: English
Status: Completed
Published: 2019-11-29
Updated: 2019-12-22
Packaged: 2021-02-26 06:08:09
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 6,675
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21598915
Author URL: https://archiveofourown.org/users/kokomocha/pseuds/mocha
Summary: You gotta catch 'em all.Second Person POV: Male Pokemon Trainer.
Relationships: Kabu/Male Pokemon Trainer, Kabu/Original Pokemon Trainer(s), Kabu/You, Rurina | Nessa/Male Pokemon Trainer, Rurina | Nessa/Original Pokemon Trainer(s), Rurina | Nessa/You, Yarrow | Milo/Male Pokemon Trainer, Yarrow | Milo/Original Pokemon Trainer(s), Yarrow | Milo/You
Comments: 13
Kudos: 179





	1. grass gets ass

**Author's Note:**

> fucking hell im so sorry
> 
> please

**Summary for the Chapter:**

> Gym Leader Milo has a hot hookup with you one night.
> 
> Second Person POV: Male Pokemon Trainer.

"Mph..."

You were tangled in a desperate makeout session in the room of his little house over the hill overlooking Turffield, the only light from the white moon that shone through the dirty window. His bedroom smelled like lint and fur but you didn't care much. You lay on the plush queen-sized bed with the Gym Leader atop you as he used one hand to pin you down by the wrist, another hand to move your jaw aside so he could kiss your neck softly.  
You let out a grunt and felt a surge of pure arousal coarse through you, straight down to the tent in your jeans.  
You were already stiff as a board down there. You kept telling yourself to hold on and hold back to make it last longer, but you couldn't help that you were such a hornYamper and that it'd been forever since you'd gotten off (jacking off in a tent next to your Pokemon felt morally wrong). “M-Milo…” You stuttered, failing to hold back a guttural moan. He placed his knees in the space between your spread legs to gain more balance.  
“Yes?” You felt his smile against the flesh of your collarbone as he trailed his kisses down. He wasn’t expecting a response. But he was going to get one and you knew it.  
He pressed his knee down on the front of your jeans as he continued to kiss your body. You moaned in desperation. The pressure was intense, but it wasn’t enough. Nowhere near enough.  
Milo traced fat warm fingertips up your shirt as he pulled the garment off you, yanking it past your head and tossing it somewhere across the room.  
He began to suck on your pectoral like his life depended on it, biting the flushed flesh to work in a purple hickey. His palm moved down to massage the growing tent in your pants, and you stifled a helpless groan.  
He slowly moved his lips to nibble on your earlobe as he whispered breathlessly, “I’ve wanted to breed you so badly… and I’m gonna till you can’t walk straight. I’m gonna use you ‘till my heart’s content.”  
You bucked into his palm as you choked on another moan upon hearing those delicious words.  
There was nothing more you wanted right now than to feel him inside you. He released your wrist to allow you to remove your shorts, and you peeled them off excitedly, pushing them absentmindedly off the bed. A spot of precum made its mark on the front of your briefs. Milo licked his lips impatiently as he, in turn, removed his clothing down to his boxer briefs, carelessly tossing his Gym uniform aside. He needed them off and away.  
Milo hopped atop you again, a husky, warm silhouette that made you shudder beneath it.  
You knew you liked girls. But this was a whole new attraction. Sure, you'd been denying your crush on your rival Hop for all these years, but, like, that didn't make you "into guys", right?  
Doing this though... probably meant you were into guys...?  
Fuck it, you liked men too.  
“I-I feel like a Wooloo in heat,” he groaned, “I can’t even think straight. It’s been forever since I been this riled up.”  
You smiled in return, palming yourself through your briefs.  
He softly tittered as he bit his lip, “I can’t take it anymore. I’ve gotta be inside you,” he pulled the waist of his boxer briefs down to his knees, and you watched as a massive, girthy cock sprung from its confinement.  
Oh fuck.  
“Th-That’s not gonna fit in me, Milo,” you stammered as your cock twitched beneath your briefs.  
“If you don’t want to do this, it’s ok,” The Gym Leader smiled softly as he wrapped one blocky hand around his member, slowly stroking it.  
You shook your head. “I’ll be ok. We can make this work.”  
You gulped and pulled down your own undergarments, allowing your cock to spring forward and bounce. With one hand you scooched your briefs down your legs and off your body, the other you stroked your sensitive head with. You couldn’t bear to go without stimulation right now. But you were also terrified of his cock ripping you apart.  
Milo smiled again as he reached beside you to the drawer in his bedside desk, fumbling, pulling out a bottle of half-used name-brand lube. Guess you weren’t the first person to have lay in this bed. Huh.  
He squeezed the cold gel onto his cock, spreading it from tip to base. He then squirted a copious amount onto his fingertip and massaged it over your puckered hole, and you winced at the cold touch, arching your back slightly. Milo gently worked a finger in to warm you up. Your dick quivered. It certainly hadn’t been the first time something ventured up your ass but it was the first time some*one* ventured up your ass. All those nights getting off to Hop finally paid off.  
With his other hand, Milo grabbed your cock and slowly, painfully, torturously stroked you in tandem with his now duel-fingered motions in your ass. You thrusted instinctively into his grasp, desperate for more stimulation, but he refused to budge.  
Milo stopped after a few moments of sweet torture, resetting himself onto his knees.  
“Alright, babe, we’re gonna go nice n’ slow,” The Gym Leader cooed as he positioned his member at your tight hole.  
You lay on your back, staring up at the shadowed figure pressing his tip against your sensitive area. He kept balance on his knees, using both of his hands to cup your lower back to scoop your bottom half up to his height, leaving only your torso touching the mattress. You thought about wrapping your legs around his waist but decided against it. Too restricting.  
Milo pressed softly as he uttered the words, “Tell me if it hurts too much, alright? ‘M gonna be very gentle with you, I promise.”  
Before you could oblige, the head was inside you.  
You flinched and clenched your fist in pain, pursing your lips to stifle a whimper.  
He pushed. And pushed. His hands grabbed the bones of your hips, pulling you towards him.  
You bit your lip. The size was going to take some getting used to. But you refused to cry out, you weren’t some beta male who couldn’t handle multiple inches of cock inside him. And you wouldn’t let Milo see weakness.  
He pushed and pushed, inches of girthy meat disappearing into your puckered hole, surrounding his cock with hot, pulsating flesh.  
And his hips touched your butt. He was all the way in.  
“S-See? Not so bad, right? I’m proud of you for taking it all,” he smiled softly. You could tell he was really restraining himself, the way he clenched his jaw.  
You chuckle in return. “F-Fuck, Milo, you’re real big…” He squished the muscles of your thigh in return, causing your dick to twitch oh-so-wonderfully.  
“Gh… God, you feel so good, it’s… My head is spinning….” he responded, trailing off with a slew of restricted grunts.  
You lick your palm and move your hand to your member, grabbing it and choking it, squeezing your fist over your sensitive cock, then back down to the base of your cock, barely touching your aching balls.  
Milo swallowed a groan as he slowly pulled out of you. You winced in response to the unexpected feeling of absence in your rectum. Not that his presence was comfortable by any means, it was just that you were ready to embrace it.  
Halfway out Milo stopped.  
You locked eyes with the half-lidded, painfully aroused Gym Leader, and his cheeks were flushed, his jaw clenched, his breath labored.  
“I-I-I’m sorry, I can’t-I can’t, I-” Milo stuttered between guttural pants, and you didn’t have time to question his words before he slammed back into you, squeezing the flesh around your hip bones as he groaned in relief.  
You helplessly yelled in pain, gasping and gripping the bedsheets after releasing your cock from your clutch, watching it bounce as the Gym Leader relentlessly pounded into your asshole, iron grips on your hips as he used your thin body as a fucktoy, pulling you closer and closer to his own hips before pushing you away in response to his desperate thrusts. Tiny tears began to roll down your face as you bit your hand to restrain the cries of pain.  
Milo’s fingernails dug into the flesh of your hips as he fucked you, drowning in the feeling, his eyes squeezed shut and his eyebrows furrowed in concentration. His stifled moans countered your loud, trembling gasps.  
The lube helped lots. Milo slid rapidly in and out without friction, and as you gulped down heavy, shaky breaths, you began to relax a bit by bit.  
You swallowed the lump in your throat as you felt the head of Milo’s cock brush up against something peculiar.  
Again. And again. And again. And again.  
You began to relax even more, loosening your once-frigid muscles.  
And suddenly you were softly groaning too, drool lightly spread across your tear-stained cheek as your hand shakily moved from your mouth back down to masturbate, the other hand still gripping the sheets.  
“Gh! F-Fuck! Ah!” Milo’s grunts were soft but plentiful, and they were music to your ears.  
You moaned pleadingly as his cock rubbed against your prostate. The building feeling of an orgasm was rushing up, growing, blooming. The hand glued to your dick was a rapid blur; you jerked relentlessly and with only one objective in mind.  
His motions became faster. Your body was being so roughly used but you were in love with it.  
You felt like a ragdoll. Milo’s speed indicated that he was close to orgasm, too, and his breathy grunts told the same story.  
You locked your legs around his hips and he fell to the mattress, releasing your hips and moving his hands to the spaces on either side of your upper torso, scrunching folds of green comforter in his hands as he leaned and towered over your body, pressing everything he had into you as he came. The mattress bounced beneath you in response to the pushes against it, creating creaking noises that echoed through the room.  
You watched as he bit his lip to no use, because his pleading moans leaked out of his mouth like falling leaves as he rode out his orgasm, causing cum to dribble out of your stretched asshole.  
The grip on your dick softened as you came moments later, a shower of sticky semen raining over your small chest, painting your torso with cream-colored cum as you cried in pleasure.  
Milo slowed his pace and eventually stopped, pulling his softening dick out with a squelch, a thin trail of cum exiting your hole as you shivered from its absence. He pulled his boxer briefs up to his waist, a tiny dot of cum staining the front as he stood up to stretch and crack his back.  
You sighed, smiling, as your asshole winked, forcing more droplets of cum outside and onto the mattress. You sat up slowly, carefully, groaning from the pain. Milo swooped in to help you up, your legs shaky and body trembling.  
“I-I-I’m so sorry,” Milo stammered, “I just lost myself and you felt so good, I couldn’t control it, I promised I wouldn’t go rough and-”  
“-No, believe me, I like rough sex,” you spoke reassuringly, “I just hadn’t had it in… well, the ass before… But I'm fine! I promise. It... it was fuckin' hot.” Your cheeks flushed. You didn't really know why saying just that made you embarrassed considering the man next to you was plowing your fields mere minutes ago.  
Milo sighed in relief after a pause. He sat back down on the bed next to you, the mattress sinking under his weight.  
Silence.  
“Spend the night. Please,” Milo muttered, looking away. You glanced at your Rotom phone on the dresser. 12:46 am.  
You think, then frown. “I can’t. I’m sorry. I need to be heading to Hulbury early morning and I don’t want to stir you when I rise…” And you're genuinely remorseful. You would've liked to stay and spoon in his green bed, curled in his warm embrace as you two drift off to sleep. But you had a mission. And all good things had to come to an end. You couldn't have dated him, attractive as he was.  
Milo sighed deeply, “...I understand. You’re still a Gym Challenger, after all. Go on. Harvest that dream. But...”  
“But what?”  
“...” Milo turned to you and leaned forward quietly, pressing his lips against yours. He parted his lips, cupping your jaw. You rested your hand on Milo’s chest, pulling the fabric closer to you. He pulled away.  
“Y’oughta be going now, trainer,” Milo spoke softly, “...but take this with you. A token of my gratitude.”  
He handed a small piece of material to you. You decided to look at it only when you were a safe distance from his house.

The moonlight guided your path and illuminated his Rare League Card in your hand.


	2. water u waiting for

**Summary for the Chapter:**

> It's Nessa's turn.
> 
> Still Second Person POV: Male Pokemon Trainer

**Notes for the Chapter:**

> ah shit here we go again  
> male trainer does sex, that's it  
> on a more serious note, please please go check out "fix your mistakes" (https://archiveofourown.org/works/21627910) by lycanicNovelist!! it's a sequel to "grass gets ass" and i luv it and i luv them and its so good guys
> 
> nessa is a top and no one can change my mind

It had started on the couch in her lavish apartment, drinking rosé and telling small-talk stories. You couldn’t help but notice the nautical theme to her living space; marble countertops, anchor decorations on baby blue walls, an aquarium with little Magikarp, pictures of her and her Water-Type Pokemon framed. You had drank enough to make those features blurry.  
She invited you there to celebrate your win. She felt like she owed that to you.  
And you’d spent so much time in a tent with your team (nothing against them) that you couldn’t remember the last time you actually hung out with another person.  
Oh wait, yes you can.  
Truth be told, you hadn’t been able to get Milo out of your mind.  
So you’re distracting yourself with other people. But if you ended up winning this Champion thing and allowed enough time to pass… maybe you could go back to Turffield and fix your mistakes.  
But right now you couldn’t think about your last hookup. You were hanging out with Nessa, and she seemed to be having a decent time despite her resting bitch face. Her eyes squinted as she told stories of her best wins on the battlefield, sipping the light wine between each pause.  
You listened haphazardly, pouring yourself another glass. You peered at it, observing the engraved ocean waves on the cup. Damn, this Leader was committed.  
There was something on her mind. Her pauses were becoming much longer as she drank--no, chugged--the rest of the near-empty glass bottle of wine.  
You looked hesitantly into her narrowed eyes as she moistened her lips, saying, “I wanna try something with you.”  
You knew better than to refuse.  
And the next few moments were a blur.  
You remember that she stumbled, straddled you on her couch, nibbling your earlobe as she traced her acrylics down your chest, playfully flicking your nipples.  
You remember sucking on the sweet flesh of her collarbone, giving plenty of little nips around her sports bra just to tease her.  
You remember that she palmed you through your trainer shorts and you used an expert finger to rub the outside of her Gym uniform, a thin waterproof boyshort that proved to be a flimsy barrier, because the tiny moans she released as she buried her head in the crook of your neck were incredible.  
You remember that before any clothes were truly removed, she hungrily grabbed your hand and led you to her bedroom around the corner, a simple space with seafoam-color lighting and a queen-sized bed in the corner, elevated by a bedframe with intricate wave designs.  
Unsurprisingly, she had a water bed.  
And on that bed she straddled your hips, peering down at you. You felt her gaze pierce through you. Your hands gripped her bony hips as she grinded into you.  
“N-Nessa…” You mumbled. She showed no signs of weakness. No smile. No frown.  
“So we doing this or what?” The Gym Leader spoke with such an attitude that to the untrained ear, it would’ve sounded like Nessa was inconvenienced. But you dealt with her taunts on the battlefield, and you beat her Water-type team to a pulp. You were accustomed to her voice. It was an endearing tone.  
“‘Course we are, babe,” you smirked, retaliating with the same attitude she offered. You don’t really know what came over you, talking all smooth like that. Maybe it was the adrenaline. The hormones? Or maybe the rosé? Probably the rosé.  
She traced her acrylics up your shirt, rubbing past your ribs, your nipples, pulling the trainer shirt off your head. She tossed it somewhere in the room. The air was cold.  
You bit your lip.  
She looked down at you. You didn’t have abs, that’s for sure. But you pride yourself on your better-than-average body.  
She smiled faintly, then crossed her arms to remove her top, tossing it off the bed. The thin sports bra slid over her tits, and they bounced out, perky and inviting. Your hands, with minds of their own, reached up to play with them. One hand squeezed a boob, another pinched a little nipple. Nessa inhaled sharply, grinding against you harder than before.  
“Th-That…” She began.  
“That what?” You smiled devilishly.  
“... Keep doing that.”  
You smiled. “Yes, ma’am.”  
And for a second there you saw a blush rise on her face, but she hid it behind a gloved hand.  
“... Like I was saying before, Trainer, I wanna try something with you.” She mumbled. You retracted your hands.  
“Anything you want,” you spoke, too confident to pass as sober.  
She dismounted you and hopped off the bed with a squish in the mattress beneath, and you watched her disappear, dipping under the bedframe in search of something. You didn’t think too much about it.  
She rose back up with multiple objects in her hand, hidden by her shadow as she blocked the light facing you.  
Nessa straddled your waist again, and you make out the shape of a cord in her grip.  
“It’s an Escape Rope. They’ve more than one use, y’know,” she spoke softly, then growled, “... so hands up. Now.”  
...Okay. Oh fuck.  
You knew where this was going.  
You were almost afraid to defy. Your hands shot up above your head as you lay still as a surfboard, and she looped the Escape Rope around a pole in her bedframe, tying tight knots around your wrists. You tried to wiggle free but damn, she tied them good. You were fully bound.  
Ironic, an Escape Rope used to prevent you from escaping.  
You jerked your hands again.  
And again.  
And again.  
And Nessa traced her acrylics down the sides of your chest, and the twitch in your pants magnified.  
Oh, okay. Okay.  
Something was kinda hot about this. Your painful erection supported that idea.  
You guess you weren’t too opposed to being tied down.  
Her fingers ended at the elastic waist of your shorts, and she slowly, slowly, slowly pulled them down, past your feet, and whipped it behind her. It reminded you of how Leon flips his cape. Odd comparison.  
She looked at your hard-on and smiled back up at you, a small curl of the lips. A smile that made your heart race.  
Nessa used her long nails to trace over the outline of your cock beneath the briefs  
and you exhaled sharply. Her pointer finger drew soft circles on your underwear as her other hand reached to trace the head of your dick, which sputtered a meager drop of precum at her touch. Your breathing became noticeably hitched, and you bit the inside of your cheek.  
She used the pads of her fingers to rub lightly against the underwear fabric and your dick twitched painfully.  
“N-Nessa,” you blurted. This teasing had you hard enough to be considered a Rock-type.  
She looked up, narrowing her eyes in playful sass.  
“Okay, okay….” she muttered to herself as she curled two fingers around your elastic waistband. She pulled it down, and your dick sprang up in impatience, bobbing to-and-fro, aching and swollen.  
She ran one long nail up the length of your cock and it twitched, your hands trembling in their restraints as she traced over your frenulum and around the head.  
She smiled softly. And wrapped her plush lips around your bellend and twirled her tongue around, allowing a thin trail of drool to drip down your cock. Slowly, slowly, she fit you all in her mouth, giving plenty of stimulation with that magic tongue of hers. It took all the self-restraint to not thrust into her maw. But you fought even more against the rope and chewed the skin of your bottom lip as her mouth touched the base of your cock, her nose pressing up against your trim pubes.  
You could’ve cum then and there.  
But she pulled up quickly and with a slurping sound, wiping her mouth off with the back of her gloved hand, making unbreakable eye contact with predator gaze.  
You tightened the muscles in your lower body as you thrust into the air, desperate for another feel of her warm mouth.  
Another cold smile grew on her lips as she spoke softly, “Had to get you soakin’ wet before we begin.”  
She leaned over and peeled her thin shorts off, following with her seamless thong, the crotch of it already a bit damp. She tossed those aside, not caring where they landed.  
Nessa positioned and lowered herself over your dick, grabbing it with one hand and guiding your tip to her entrance, teasing the head with her warm, wet entrance. She grinded on you, rubbing herself over your cock, loving the deliciously desperate look in your eyes. She sighed contently as she allowed the head of your member to dip in slightly only to then let it slip out, pushing the pulsating cock between her lips continuously, rubbing against her swollen clit. A little moan escaped her lips.  
“P-Please!” you moaned. You weren’t used to begging. But something about this, having someone else in control…  
Your thoughts were interrupted as she slammed down on your cock, bouncing up and down, gyrating her hips so your sensitive head could feel her surrounding walls. You sat, paralyzed, and this proceeded for minutes before you regained your movement.  
You instinctively thrust back into her, and you two smacked against each other with such fervor that your orgasm was pressing against your balls.  
“N-Nessa, I-I’m about t-”  
Until her walls clamped powerfully around your cock and she moved her hips wildly, a delicate finger of hers fidgeting with her clit, her back arched and her eyes rolled into her skull as she released a sweet moan, repeating the same phrase softly, “I-I’m cumming!”  
You balled your hands into fists as you used every ounce of restraint in you to not cum in her.  
A few more moments of her riding out your orgasm and she pulled herself off you, leaning back as you relaxed every muscle in your body, releasing your cum in a spectacular shower that stained her bedsheets. You groaned as she moved her hand back to jerk you off and help you ride out your orgasm. God, all that teasing made you cum buckets.  
You struggled to catch your breath as the feeling of pleasure disappeared and you descended your high, while she slowed her pace on your cock.  
You exhaled softly and moved your eyes to her gaze. Much less intimidating. She was relaxed and content and… smiling.  
You moved against your restraints. “M-Mind releasing me?” you laughed.  
She gasped. “Right, right. Sorry,” she muttered as her hands dove behind her bedframe to loosen the knots.  
She untied the knots around your wrists and you rubbed at them in attempts to soothe the red flesh.  
She looked at them, and looked at you. You smiled at her and saw a little blush creep up her cheeks.  
After you both found your clothes scattered around her bedroom and put them back on, ignoring any wet stains, you checked the alarm clock on her dresser. 12:46 am. Huh.  
“You have to go.” She stated plainly before you could say anything.  
“Uh, okay…” Not that you were opposed, because you had to leave anyway, but because of her tone. And insistence. Kinda… hurt? You weren’t stupid, you knew this meant nothing. But, c’mon...  
She noticed the look in your eyes, “Not that I don’t want you here. Just… if you’re seen leaving my place in the morning… I don’t want you to risk being disqualified from the Gym Challenge. You’ve come this far.”  
Only two gyms, you thought to yourself. But whatever. She did have a point.  
“I get it,” you smiled. She nodded.  
“Alright.”

You turned the knob on her front door before she yelled, “Wait!”  
She walked out of her room in her usual nonchalant manner, but she held a thin piece of something in her hand.  
“Take this,” she spoke, “and… and gimme a call if you’re ever back in Hulbury. Make waves, Trainer.”

You set her Rare League Card next to you as you drifted to sleep in your tent.  
Maybe you’d call the number she wrote on the back sometime.

**Notes for the Chapter:**

> She jabbed one pointed nail into the suspicious bruise on your chest.  
> “Where’d ya get that from?” she giggled, a glint in her eye.  
> “Uh...Uh….” Ok, so you probably shouldn’t tell her that you fucked a guy two nights ago. And he left mad hickeys.  
> “Milo did that, didn’t he?”  
> You blushed. “I-I-I… No…”  
> Nessa laughed. “It totally was, wasn’t it?”  
> You grew silent.  
> “He’s been actin’ weird lately. Did you dick him down hard or somethin’?” she stifled a giggle.  
> You didn’t bother telling her it was the other way around.


	3. playing with fire

**Summary for the Chapter:**

> Kabu has a round with the trainer.
> 
> Second Person POV: Male Pokemon Trainer

**Notes for the Chapter:**

> ohhhhhhhh my fucking god
> 
> back on my bullshit, sowwy for my sporadic updates i just been busy with skool
> 
> anywhomb im finished with the game and close to finishing the dex!! 
> 
> and i didn't like kabu at first but i liked writing this bc it required me to do some research on him and it was fun finding stuff out!! i actually really appreciate his character now!!
> 
> also the puns/references as the chapter titles has started to make my cringe but i must continue the legacy

He was stoic.  
That’s the first thing you really noticed about him.  
You two sat on his leather couch. He had a beer, he insisted on giving you a root beer. Legal drinking age was 16 in Galar, and you had passed that, but he refused to allow it.  
You noticed the wrinkles in the space between his eyebrows from furrowing them so often. His soft, wispy grey hair fell above his dark eyes. Now, he was relaxed, eyes squinted, locked with the fireplace you two sat before. His fingers fumbled with the tab on his canned beverage, and he licked his lips quickly. They looked soft.  
You snapped your eyes shut and shook your head. Don’t. Don’t do this. You had gotten lucky with the past two Leaders. Plus, Kabu’s like… old. Not in a bad way. He’s rugged and handsome. But him inviting you to his place did not mean… anything. He probably just wanted to talk strategy with you or some shit.  
Kabu turned to you.  
“I invited you to my household because I plan on talking strategy with you. You were able to take me out with your Drizzile and its Water-type attacks easily, but the opponents in your future, and certainly not Leon, will be nearly as type-focused. You cannot depend on having an advantage at all times. You need to think smart.”  
You listened intently. He had some good points.  
But after a few minutes of him rambling on about Dynamax benefits and taking the opponent by surprise you began to lose interest and tune him out. Your mind was lost in thinking about anything else.  
You were back in Motostoke for the first time since you left to acquire your first Gym badges. You’d almost forgotten just how large and daunting it was. And how different the city felt than the last two you had been in.  
Nessa’s card was tucked neatly with Milo’s card in your wallet. If anyone found out about this, you’d definitely be a dead man. You’d be revoked of your challenger status and accused of using your body to sway the Leaders. Or something. But it made you a bit excited, the feeling of almost being caught. Not that you would be found out, but it shot adrenaline through your veins just thinking about it. Going against the rules.  
You were contemplating whether or not you should tell Hop about your experiences. You’d at least tell him about Nessa… Maybe not Milo. Yet. Because Hop didn’t know everything about you. He didn’t know the extent of your orientation. And as much as you hated to admit it, you still liked Hop. Like… Really liked him. You wanted to see him. But you couldn’t, and you still had committed to becoming champion after beating the fellow competitors. You couldn’t wait to defeat Marnie and that bellend Bede.  
“Are you even listening, Trainer?!” You shot up to attention as Kabu barked at you. You could tell by his twitching eye that he was losing patience.  
“Y-Yes, sir.” You muttered.  
“Good,” he added with a pause, “repeat back what I’ve told you.”  
“Uh.. something about…” you paused for a moment, thinking about when you started tuning him out, “taking the opponent by surprise?”  
Kabu crossed his arms and nodded, eyes closed.  
A grey hair of his bounced forward, over his eyes. He opened his mouth slightly to blow it back over his head. But it fell right back down.  
It was adorable.  
And your heart skipped a beat.  
Your eyes trailed down his athletic build, noticing the muscles beneath his uniform.  
Your brain entered horny mode.  
What? You were a young guy. Still raging with hormones.  
Fuck it.  
“So, you’d want me to take... you by surprise?” You spoke softly, a hint of flirt in your voice. You weren’t sure what possessed you to say that, but… What was the worst that could happen? You weren’t thinking about the future. If Kabu rejected you, then you’d live with it. It’s part of life.  
“Yes. That is one way to really tackle your opponent. Do something they won’t expect, and they will bend to your every whim.”  
You began to scoot closer to him, looking away, smiling softly, “You mean it?”  
Kabu looked at you, frowning, arms still crossed, “Of course I mean it! That’s how you win someone over!”  
In an act almost automatic, you extended a finger to Kabu’s knee, slowly circling his kneecap, tracing up his thigh slightly, “So if we were in a battle now, you’d want me to do something that would keep you on your—” you slid your fingers over the fabric of his shorts and up, up, up his thigh to touch his hip— “toes?”  
He stiffened.  
You looked up at him innocently.  
He straightened his back, clearing his throat, “I-I suppose I would want that. Makes for an interesting battle. But you wouldn’t win against me.”  
You smiled cheekily, “You don’t think?” Your fingers traced his inner thigh and you felt his muscles tense up.  
You trailed one dainty fingertip over his length, barely enough for him to even register, and you heard a choked grunt from the back of his throat.  
He was still closing his eyes. His hands fell to his knees as he hunched over, squeezing at his kneecaps. You looked at the landing spot for your prying fingers and sure enough, he was stiffening.  
“N-No, I don’t think you’d win,” he muttered through gritted teeth.  
You used two gentle fingers and traced squiggly lines over his thigh as you heard the man stifle shallow breaths as his eyes remained shut, your fingers moving closer, closer, closer—  
Kabu shot up, straightening his back, eyes wide open. He gulped.  
It was incredible to see him like this. Pent up, but never succumbing. His strategies not only lay on the battlefield, Kabu was a stern stone of a man in general. Not to say that he wasn’t kind, you’d seen his performances on the telly, the was he connected with his Pokemon was so raw and real. But he was stoic and serious… You’d never even seen him smile. And that’s exactly what made this so fun. You wanted to push him to his limit.  
How far could he go?  
How far could he be stretched before he melted in your hands?  
Kabu slammed his eyes shut. You palmed his cock through his shorts lightly, not enough to provide substantial stimulation but enough to leave him begging for more.  
“W...What are you trying to do?” he muttered.  
You smiled. You already had him in your clutches. “What do you want me to do?”  
Kabu exhaled sharply, half-lidded eyes speaking more than words ever could.  
And though one hand stayed glued to his knee, the hand closer to you grabbed the top of your thigh with such force that you jumped at the touch.  
Oh?  
Your palm moved back to the junction of his inner thigh and his member, pressing fingers into the tough skin over the fabric of his shorts as you saw him restrain himself from jolting. He moved his hand in turn, tracing up your thigh with his entire hand, squeezing at the meat. You continued to tease him, rubbing the base of your palm at the sensitive crease. He used one finger to trace over your hardening cock.  
You two still did not look at each other, filling the room only with shallow breaths.  
Until you made the decision to turn to him. You moved your body to face him, scooting closer as he rested his hand on your thigh.  
He turned to you, a tired, desperate glare behind those dark eyes, heavy breathing.  
God, that was hot.  
He remained with an iron grip on your leg, still watching you with hungry eyes, when the best idea hatched in your brain.  
“Let’s play a game, since you like competition so much…” your words were coy and honeyed.  
He blinked and parted his lips in shock before speaking, “What game?” It came out as more of a demand than a question.  
You smiled as you stood halfway up from the couch to shimmy your shorts and briefs off. The air was warm, but you still shivered as your dick bounced from its confines, swollen and needy. You were way too drunk on hormones to be nervous, whipping your cock out in front of a much older, much more dignified male. And you weren’t “big” by any means. You were average, maybe above average if you were really rarin’ to go.  
And, well, you were.  
Kabu turned white. You began your explanation, "The first to cum loses," but paused for a moment, suddenly nervous that he was going to turn your advances down.  
But he stood up quietly, closing his eyes and exhaling harshly, exposing you to the thick outline of his erection, leading you to place your hand on your own. He yanked down his uniform shorts, followed by his red boxer briefs, and out popped his girthy uncut cock sprouting from a thrush of greying hair, trembling from the arousal he felt.  
He sat back down next to you, almost unsettling with the eye contact he made as he quickly moved strong fingers to the base of your cock, causing you to flinch at the sensation.  
He sighed, half-smiling in disbelief of his actions.  
You took that as the signal to lick your palm and move to his cock. You noticed how warm it was as you wrapped your slick fingers around the middle of it, pulling down to expose his flushed head from its layer of untrimmed skin. You’d never seen an uncircumcised cock before. This was interesting.  
“Okay,” you broke the silence.  
Kabu coughed.  
“R-Ready, set…”

But you were cut short as Kabu began to jerk your cock, removing his hand for only a split second to spit on his palm. You snapped to it and began to rub him too. You two dare not break eye contact as the only sound in the room was the pleasant squelching of spit-lubed fingers shaking swollen members. You held your breath to not let him hear anything remotely sounding like a moan, and you noticed his breaths were incredibly slow, the slight shaking between overwhelming moments. You both were frantic with arousal coursing through your veins, but neither of you would dare show it. The only thing you would show was the blurred motion of desperate hands jerking desperate cocks.  
His eyes narrowed after you smirked, hearing his breath falter as you quickened your pace. As revenge, Kabu’s iron grip slid over the top of your dick as he twisted his hand around, rubbing your sensitive head as you unintentionally thrust into his hand, releasing strained groans. You had jacked him off with certainty at first but now your tugs on his cock were shaky and unsure; the way he pulled on yours made your mind grow numb and your hands forget how to move.  
Snap out of it, snap out of it, he’d win at this rate!  
But damn, was he good. He stiffened the muscles in his lower arm and forced them to twitch to create a vibration-like feeling on your cock, and you almost melted then and there.  
Maybe you flew too close to the sun with this. You felt like you were losing your mind. Your grip was loosening on his cock as his only tightened on yours.  
You began to feel the familiar surge of an orgasm building up at the base of your member.  
Any trace of coherence in your mind was absent. You’ve pretty much lost, you thought to yourself, as your hand slipped from his cock.  
Trainer snapped out of his confusion!  
You shook your head and tightened the muscles in your groin to somehow preserve the orgasm building and to lessen the focus on the pleasure he was providing you. Kabu looked up into your determined eyes.  
Your hand, after being licked liberally, locked onto his cock and jerked like your life depended on it.  
His grip loosened at the surprise of your stimulation.  
You took that split second of his guard being let down to lean over, covering your cock with your body, and take his length in your mouth.  
You sucked the tip at first, and you heard Kabu sharply inhale as he placed his arms behind him for extra support in a lapse of judgement, forgetting the objective of the jerk-off game, abandoning your cock for his own. You knew he’d crack sometime.  
His thick member slid down your throat with ease as you bobbed your head back and forth, using one hand to fondle his balls. Your tongue thrust its way beneath the hood of his cock, lapping at his sensitive head, flicking your tongue in and out as you squeezed his length down your throat, ignoring your gag reflex as much as humanly possible.  
Kabu began to thrust into your mouth as one hand of his grabbed the back of your head to further push you down on his dick. Your eyes widened as you gagged, but you resumed the blowjob. Your mouth was getting tired, so you alternated between swallowing his cock and jerking him off rapidly, thankful for the spit your mouth provided to lube him up.  
You used one hand to pull his skin down to trace his frenulum with your tongue and he bucked into your mouth, slamming his hand against the back of your head and forcing your nose against the thrush of grey pubic hair as he growled loudly. You felt the warm flow of semen dribbling down the back of your throat, his cock twitching furiously in your mouth as you used your tongue to massage the bottom of his rod. His hand held curls of your hair in a tight embrace, riding out his orgasm as he slowed his thrusts, pulling out eventually. You watched as a thin strand of cum connected your bottom lip to the head of his softening cock, and the only sounds came from the blood rushing in your ears and Kabu’s heavy breathing.  
You sat up. Looked at him after a moment. His breath was slowing down.  
As you locked eyes with the exhausted Gym Leader, you smiled, gasping, “I win.”

It was around half-past seven leaving his place. The lampposts of the quiet Motostoke street illuminated your way back to the hotel and the holo foil of Kabu’s Rare League Card, displaying both his phone number and a much younger picture of him, still sporting the same determined look.  
You laughed to yourself.  
He was still hot.

**Notes for the Chapter:**

> https://www.youtube.com/watch?v=XKPCTckAgqE&list=PLpMERZJf4zPVrUov5MlbLP7vHF53BExCg&index=9
> 
> also i really like the idea of trainer being a cocky little shit hehe


End file.
